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I’ve listed Hampden-Sydney again this year as the most preppy college in the South. It was founded in 1775, when George III was King of England, Virginia was a British colony and the Declaration of Independence was yet to be written. One of only four all-male colleges remaining in the United States, Hampden-Sydney counts Patrick Henry and James Madison as two of its original Board of Trustees members.

Phi Gamma Delta Fraternity Members at Hampden-Sydney College

Students at Hampden-Sydney take a great deal of pride in their appearance and believe in good manners. In fact, the school has published its own etiquette guide: To Manor Born, To Manners Bred (now in its 7th edition), which has been updated for the social media age. That’s serious dedication! Some gentlemen of Phi Gamma Delta fraternity above display a range of attire: plain front khakis, blue blazers, a navy suit with a Brooks Brothers repp tie, freshly pressed pinpoint and oxford cloth button downs, bow ties, ribbon belts with motifs and a needlepoint belt. This is all standard dress on campus, and one of the reasons Hampden-Sydney is considered a very traditional college.

Hampden-Sydney Alumni Tailgating Prior to a Football Game (Fall 2012)

In the February 2013 issue of Town & Country, Hampden-Sydney alumni were featured tailgating on campus prior to a football game against arch rival Randolph Macon. All of these gentlemen are sporting bow ties, and one is wearing Nantucket Reds with a pair of go-to-hell socks that would make President George Herbert Walker Bush envious. Tailgating was spoofed in Lisa Birnbach’s The Official Preppy Handbook (1980) in which she also listed Hampden-Sydney as the #3 preppy college in the country behind Babson (#1) and Hamilton (#2).

Off The Wagon: The Tailgate Picnic – The Official Preppy Handbook

Also in The Official Preppy Handbook, noted both for its finely drawn satire and anthropological treatment of preppies, is a section on body types with representative photos and descriptions of each. The Good Old Boy’s biography includes attending Lawrenceville and Hampden-Sydney, and his stated attributes suggest a fun-loving, if not bawdy, demeanor. He is holding a “genetically attached beer can,” while wearing a button down layered over a Lacoste shirt (Southern collar notably not popped), rumpled, flood level khakis and a pair of penny loafers, one of which is duct taped to keep the sole and the upper together – a practice cultivated at Lawrenceville. He’s the one of the three I think I’d most enjoy being around.

Body Types (Male) – The Official Preppy Handbook (1980)

As an homage to Birnbach, whose publication became a national bestseller, the college’s Kaleidoscope yearbook staff responded with The Official Preppy Yearbook.

Birnbach visited Hamden-Sydney a few years ago to promote her most recent book, True Prep, in which she elevated the college’s sartorial place, writing,”… allow us to assure you, in no uncertain terms, that Hampden-Sydney is, without equivocation, the preppiest college in the United States.” In fact, one enterprising student there, Samuel Thomas, recently co-founded a bow tie company called Dogwood Black (originally Southern Ties) and is now marketing his expanding product line nationally after getting requests from upscale men’s clothiers.

Dogwood Black: Nantucket Summer Madras Bow Tie

In addition to the classic madras bow tie shown above, Dogwood Black offers such unique items as a camo bow tie. I think this qualifies as the Southern version of go-to-hell style, allowing a wearer to go from duck blind to formal party without skipping a beat. One quote on the company website functions as a philosophy about wearing one of their ties, “If you can handle being the center of attention.”

Dogwood Black: Camo Bow Tie

Dogwood Black – Tie Box

Hampden-Sydney has become more diverse in recent years, and with that change has come a difference in fashion sensibility on campus. The look among some students retains the preppy style but is much more updated. The gentleman on the right (below) looks as if he might be wearing a Dogwood Black Delta Chifraternity bow tie, but I’m not positive. The gentleman on the left seems more aligned with Unabashedly Prep, which I’ve heard described as “new wave prep” or as “preppy with a twist.”

Preppy With a Twist at Hampden-Sydney

Dogwood Black – Delta Chi Fraternity Bow Tie

Dr. Christopher B. Howard, Hampden-Sydney’s 24th president, is a graduate of the U.S. Air Force Academy. This gentleman was a Rhodes Scholar at Oxford University, where he earned a Master of Philosophy and a Doctorate of Philosophy in Politics. He also holds an MBA from Harvard Business School. Howard is the first African-American president in the college’s history, and he is proudly a Brooks Brothers man.

In 2010, Hampden-Sydney entered into a formal partnership with Brooks Brothers to provide a 15% corporate membership discount to students, faculty and staff of the college. The program is titled “Dressing for Success with Brooks Brothers.” In this YouTube video, President Howard discusses the program and the investment in college education with parents of prospective students at an event hosted in a Brooks Brothers retail store in Richmond, VA.

Hampden-Sydney Display at Brooks Brothers in Richmond, VA

Now in its third century of operation, Hampden-Sydney has a beautiful campus, an excellent academic reputation, a long tradition and a very loyal alumni base, many of whom contribute substantially to the institution every year. Its past is distinguished, and its future looks secure.

Portrait of me with my cousin, Brandon, in 1986. He was not quite a year old when this photograph was taken. I was a sophomore at Wofford College at the time. My look hasn’t changed a lot since then…well, at least the clothes, because I now sport a shaved head and a goatee. Here I am wearing a wool argyle sweater from Brooks Brothers, a blue oxford cloth button down shirt and P3 tortoiseshell glasses. A few years ago, Brandon got his master’s degree from NYU and now works in marketing for Madison Square Garden. He’s getting married next spring. Time goes too fast!

I have a very old sweatshirt from the Yale Co-opthat I bought as a grad student in New Haven in the early 90s. It is full of small holes here and there and is fraying badly on the collar and cuffs. It’s 100% cotton – very soft – and I wouldn’t part with it. I’ll wear this sweatshirt until it falls apart. Unfortunately, the Yale Co-op, which served generations of students, is no longer around. They had to file for bankruptcy in 1999 and went out of business the following year.

This shot was taken with a forward facing camera on my iMac, using Photo Booth, and then modified with the oil paint filter in Photoshop, experimenting with a few things there, I guess. Also visible is the collar of a frayed Brooks Brothers button down shirt (thrifted: $2.50). I have on a Timex watch with a red, white and blue striped grosgrain band from J. Press and a pair of P3 “tortoise shell” (acetate) glasses from Coastal.com. They have great deals on glasses. I got the frames with progressive lenses and had them shipped for a total of $149.00.

My wife took this photo of me looking at books among the vendors at Union Square near 17th Street in New York City. As best I can recall, this was taken around December of 1997. We had been in the city nearly a year, having moved up from South Carolina, and I was working for MoMA.

Union Square was a seven minute subway ride on the L Train from the Bedford Avenue stop in our neighborhood: Williamsburg, Brooklyn. The World Trade Towers are visible to the right, just beyond the pedestrians. Washington Square Park was a short walk south down University Place in the direction of the towers.

My sartorial style was largely out of synch with the burgeoning hipster population of Williamsburg, but drew respect from our old school Italian neighbors. In this photo, I was wearing charcoal gray wool flannel pants, a button down shirt, a wool argyle sweater (non-thrifted Christmas gift) from Brooks Brothers, a wool herringbone pattern topcoat and a pair of black Bass Weejuns. The glasses were tortoise rim.

I’m not sure whether to love or hate the fact that hipsters have appropriated (maybe hijacked is a better word) the preppy look in the last few years. They are certainly dressing better. I suppose that is a good thing. So I won’t complain too much about their “preppy with a twist” aesthetic. How ironic! When walking down Bedford Avenue once in the late 90s in khakis, a ribbon belt and a pink button down, I felt as though I was doing a perp walk based on the scornful looks I received. That preppy has been embraced by the same kind of people proves good taste never really goes out of style, even if for them it is a fad. You can read more about hipsters on Free Williamsburg. (Note: after I made this post, I found this related article published in The New York Times: “How I Became a Hipster.”

On the same day as the Union Square photo, my wife and I went uptown to see a Broadway show at the Neil Simon Theatre. I can’t remember which show it was. Maybe I can track that down by going through some old playbills. A Christmas tree is visible on the balcony above the Russian Samovar restaurant next door to the theatre.

A Madras plaid tie makes a sharp addition to the summer wardrobe. The one I’m wearing is from Ralph Lauren. I bought it last spring for $6.99 at Unique Thrift Store in Riverdale, NY. The retail price of the tie was about $67.99. Patches, our border collie, decided to do a walk on in this photograph.

Breakdown on the rest of the clothes, a combination of eBay bidding and thrift store purchases:

eBay

Brooks Brothers blue blazer: 3-button, undarted, sack cut with natural shoulders for $76.00 vs. $598.00 retail. This is the only blazer design I’ve ever worn, and it took several weeks of eBay monitoring to find one at the right price. I would have preferred a J. Press blazer, but people don’t part with them that often. This blazer is in perfect condition with no signs of wear. The lining looks brand new.

Ralph Lauren buckle back khakis: 100% cotton, plain front with 1 and 3/4 inch cuffs for $19.99 vs. $125.00 retail. Buckle back khakis were worn for a brief period in the 1950s, if I recall correctly.

1999 – A professional headshot of me taken by a photographer in Tribecca when my wife and I were living in New York City. I took my glasses off for this shot because the lenses, as I recall, didn’t have an anti-reflective coating, and because the photographer was going for more of an intense lawyerly look. I have on a Ralph Lauren navy blue wool suit with gray chalk stripes that I bought for $50.00 at a thrift store in Asheville, NC. It was memorable because, though a great suit, it was one of the most expensive thrift purchases I’ve ever made, but I still wear it occasionally. I’m not sure where I got the button down shirt and foulard tie. Both were likely thrifted.

1999 – My beautiful wife and I on our wedding day outside her aunt and uncle’s house. They hosted the reception. I have on a charcoal gray suit with suspenders, a paisley tie with navy background and a white button down shirt.

1999 – Outside the small Episcopal chapel where our wedding ceremony was held in Greenville, SC. I think my wife looks lovely here! Opting for simplicity, we kept the invitation list to 50 and had no groom’s men or bride’s maids, just a priest, a crucifer and musicians. We designed and printed our wedding announcement and program for the ceremony and asked that there be no gifts (though this was largely ignored). We tried!

The coup in the do-it-yourself approach was my wife’s wedding dress. While we were in New York, she selected her own material from a shop in the Garment District and took it to a boutique in Williamsburg, Brooklyn. She asked them to design a party dress, which cut the cost down considerably. The cap toe dress shoes I’m wearing with the charcoal gray suit were polished, but cracked, and had a small hole on one of the soles – likely visible to our guests when we knelt at the altar.

We’ve been happily married for 13 years. As we look back on the wedding, we’re glad that we kept it a simple ceremony. The organist was wonderful. There were solos from a friend who was a professional opera singer. A string quartet of classically trained musicians, my wife’s friends since childhood, played for us. It couldn’t have been a more prefect day.

1998 – My wife-to-be and I on the balcony of a friend’s apartment in New York City. You can’t tell here, but we were on the 44th floor high above 9th Avenue near Times Square. We had been invited to a Christmas party. I have on a wool houndstooth sport coat, a sage turtleneck and a pair of khaki pants. My wife is wearing a vintage (60s) green and black houndstooth jacket whose design was very Sherlock Holmes. That was a thrift find at Anne Merchant’s Time Warp shop (now out of buisness) in Greenville, SC. I still have that jacket, too.

1993 – With friends in Upperville, VA after the fall Piedmont Hunt Point-To-Point races. I’m wearing a light windbreaker, a classic Norwegian Fisherman’s Sweater from L.L. Bean, a pair of rumpled khakis – rumpled being their usual state – and Bean Boots. Among my friends is a sampling of Barbour, Burberry and Brooks Brothers.

Andy Warhol, the son of Polish immigrants, left his hometown of Pittsburgh and arrived in New York City by train in June 1949 with $200 dollars in his pocket. He had just graduated from the art program at Carnegie Mellon and wanted to work as a commercial illustrator for a magazine publisher. But he was also obsessed with becoming famous. He really wanted to be a fine artist, but wasn’t sure how to make a living at it. In fact, he was unsure whether that was even was possible.

Warhol’s first job was working for Glamour Magazine, which was one of the Conde Nast publications. He was hired by the art director there, Tina Fredericks, to do illustrations for a story called, “Success is a Job in New York.” Fredericks wrote of her first meeting with this curious looking person in tortoise shell glasses,

“I greeted a boy with a big beige blotch on his cheek, possibly going all the way up to his forehead. He was all one color. Weird. There seemed to be something other earthly or offbeat, different, for sure. Elfish. From another world. He had a breathy way of talking. His voice was slight, unemphatic, whispery, covered over with a smile.”

As a child, Warhol had suffered St. Vitus Dance, a neurological disorder that left his skin permanently discolored. He would remain highly self-conscious his entire life about his physical appearance, famously choosing to wear an outlandish gray wig when confronted with thinning hair.

During the 1950s, Warhol became one of the most sought after and well-paid illustrators in Manhattan. His increasing income allowed him to move into his own townhouse. He began to shop for his clothes at Brooks Brothers. For the remainder of his career could be seen, even during the psychedelic days of The Factory in the 60s, wearing a Brooks Brothers suit and button down – sometimes with a repp tie. He apparently ceased wearing bow ties after the 50s.

Unsatisfied with his commercial success, Warhol longed for something more. He wanted to get exhibitions in important galleries. Presenting his portfolio of drawings, he was rejected time after time – partly because his work was representational in an artworld dominated by abstraction, and partly because of his homoerotic themes, which were taboo back then.

By 1956, the only venues willing to show Warhol’s work were Serendipity, a popular ice cream parlor on the Upper East Side that was also a meeting place for gay men, and the Bodley Gallery next-door. He did not sell a single drawing. Two years later, artists Jasper Johns and Robert Rauschenberg, breaking with the dominant mode of Abstract Expressionism, laid the foundation for Pop Art with their sensational one-man shows at Leo Castelli Gallery.

Warhol’s work was maturing, moving toward a critique of consumer culture and mass production (best represented by his Campbell’s Soup series) in which all traces of the artist’s hand – brush work, dripped paint or process – were eliminated. In November 1962, his one-man show at Stable Gallery in New York City took the artworld by storm and established him as the leading figure of contemporary art. It was instant celebrity. Warhol was on the way to becoming a superstar, one of the most important artists of the 20th Century.